(5S)-benzyloxycarbonylamino-3,3-bis-tert-butyloxycarbonyl-6-hydroxyhexanoic acid tert-butyl ester

Base Information

Chemical Name:(5S)-benzyloxycarbonylamino-3,3-bis-tert-butyloxycarbonyl-6-hydroxyhexanoic acid tert-butyl ester
CAS No.:912354-33-7
Molecular Formula:C₂₈H₄₃NO₉
Molecular Weight:537.651
Hs Code.:

Synonyms:(5S)-benzyloxycarbonylamino-3,3-bis-tert-butyloxycarbonyl-6-hydroxyhexanoic acid tert-butyl ester

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Chemical Property of (5S)-benzyloxycarbonylamino-3,3-bis-tert-butyloxycarbonyl-6-hydroxyhexanoic acid tert-butyl ester

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Technology Process of (5S)-benzyloxycarbonylamino-3,3-bis-tert-butyloxycarbonyl-6-hydroxyhexanoic acid tert-butyl ester

There total 7 articles about (5S)-benzyloxycarbonylamino-3,3-bis-tert-butyloxycarbonyl-6-hydroxyhexanoic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

: 912354-31-5
(4S)-2,2-dimethyl-4-(2,2,3-tris-tert-butoxycarbonylpropyl)oxazolidine-3-carboxylic acid benzyl ester

: 912354-33-7
(5S)-benzyloxycarbonylamino-3,3-bis-tert-butyloxycarbonyl-6-hydroxyhexanoic acid tert-butyl ester

Guidance literature:: With bismuth(III) bromide; In water; acetonitrile; at 20 ℃; for 10h;
DOI:10.1021/jo061037q

Reference yield:

: 873310-64-6
2S-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethylene)-malonic acid di-tert-butyl ester

: 912354-33-7
(5S)-benzyloxycarbonylamino-3,3-bis-tert-butyloxycarbonyl-6-hydroxyhexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 90 percent / H₂ / Pd/C / methanol

2.1: NaHMDS / tetrahydrofuran / 0.67 h / -78 °C

2.2: 90 percent / tetrahydrofuran / 5 h / -78 °C

3.1: 93 percent / BiBr₃ / acetonitrile; H₂O / 10 h / 20 °C

With bismuth(III) bromide; hydrogen; sodium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; water; acetonitrile;
DOI:10.1021/jo061037q

Reference yield:

: 133464-37-6
(4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

: 912354-33-7
(5S)-benzyloxycarbonylamino-3,3-bis-tert-butyloxycarbonyl-6-hydroxyhexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: LDA; HMPA / tetrahydrofuran / -78 °C

1.2: 80 percent / Ac₂O; DMAP; pyridine

2.1: 90 percent / H₂ / Pd/C / methanol

3.1: NaHMDS / tetrahydrofuran / 0.67 h / -78 °C

3.2: 90 percent / tetrahydrofuran / 5 h / -78 °C

4.1: 93 percent / BiBr₃ / acetonitrile; H₂O / 10 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; bismuth(III) bromide; hydrogen; sodium hexamethyldisilazane; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; water; acetonitrile;
DOI:10.1021/jo061037q